KR101413775B1 - Fluoroalkane derivative, gelling agent and gel composition - Google Patents

Abstract

The present invention provides a fluoroalkane derivative represented by the following formula (1).
R-SO₂-Ar-O-R^One (One)
(Wherein Ar represents a substituted or unsubstituted divalent aromatic group having 8 to 30 nuclear atoms and R^OneRepresents a saturated or unsaturated monovalent hydrocarbon group of 1 to 20 carbon atoms, and R represents a saturated or unsaturated monovalent hydrocarbon group of 2 to 22 carbon atoms having a perfluoroalkyl group.

Description

FIELD OF THE INVENTION [0001] The present invention relates to a fluoroalkane derivative, a gelling agent, and a gel composition,

The present invention relates to a fluoroalkane derivative, a gelling agent and a gel composition, and an electrode for an electrochemical device, an electrolyte solution for a dye-sensitized solar cell, and a carbon dioxide absorbing composition.

BACKGROUND ART Conventionally, in the field of various industrial fields (for example, paints, cosmetics, medicinal medicine, petroleum outflow processing, electronic / optics field, environmental field, etc.), gelation is performed for the purpose of solidifying, I am being used.

As the gelling agents, there are gelling (solidifying) water, and gelling (solidifying) a non-aqueous solvent and a solution mainly containing them. The structure of the gelling agent can be broadly classified into a high molecular weight type and a low molecular weight type. The high molecular weight type gelling agent is mainly used for gelation of a non-aqueous solvent, and is characterized by retaining a solid phase while swelling oil by taking oil into a molecular entangled with a lipophilic polymer. On the other hand, most of the low molecular weight type gelling agents are characterized by containing hydrogen-bonding functional groups (e.g., amino group, amide group, urea group, etc.) in the molecule and gelling water or a nonaqueous solvent by hydrogen bonding (See, for example, Patent Document 1). The low molecular weight type gelling agent is generally used as a gelling agent for water, but development of a non-aqueous solvent as a gelling agent is relatively late.

Further, a low molecular weight type gelling agent having no hydrogen bonding group is disclosed in, for example, Patent Document 2 and Non-Patent Document 1, but there are very few examples.

Patent Document 1: JP-A-8-231942 Patent Document 2: International Publication No. 2009/78268

Non-Patent Document 1: J. Fluorine. Chem. 111, 47-58 (2001)

A conventional gelling agent for gelling a non-aqueous solvent generally needs to be used in a large amount, for example, about 10% with respect to a solution, and furthermore, it is necessary to transfer it to the sol at a relatively low temperature, for example, about 30 to 40 캜, There was a tendency to go. It is economically disadvantageous to use a large amount of a gelling agent for gelling a solvent (water or a nonaqueous solvent), which means that the amount of foreign matter mixed into the gelling solvent is increased, and when a gelled solvent is used, The effect of the gelling agent may not be negligible. Further, if the upper limit of the gelation temperature is low, the shape can not be maintained due to a slight temperature rise, which may cause fluidization and leakage. Therefore, development of a gelling agent which maintains a gel state in a smaller amount and at a relatively high temperature is desired.

Further, since the hydrogen bonding property is weak, a gelling agent capable of gelling a system in which a strong hydrogen bond can not be present in a non-aqueous solvent can be widely demanded.

However, the conventional gelling agents have various problems such as a small number of gelling solvents, a difficulty in the stability of the gel, and a relatively large amount of gelling agent in the gelation of the non-aqueous solvent.

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide a novel fluoroalkane derivative capable of gelation or solidification by adding a small amount of various nonaqueous solvents, a gelling agent containing the compound and a gelling composition comprising the gelling agent, And an electrode comprising the novel fluoroalkane derivative, an electrolyte solution for a dye-sensitized solar cell, and a carbon dioxide absorbent composition.

That is, the present invention is as follows.

[1] A fluoroalkane derivative represented by the following formula (1).

R-SO ₂ -Ar-OR ¹ (1)

(Wherein Ar represents a substituted or unsubstituted bivalent aromatic group having 8 to 30 nuclear atoms, R ¹ represents a saturated or unsaturated monovalent hydrocarbon group of 1 to 20 carbon atoms, and R represents a monovalent hydrocarbon group having a perfluoroalkyl group Saturated or unsaturated, monovalent hydrocarbon group of 2 to 22 carbon atoms.)

[2] The fluoroalkane derivative according to [1], wherein R is a group represented by the following formula (2).

C _m F _{2m +1} C _p H _2p - (2)

(Wherein m represents a natural number of 2 to 16, and p represents an integer of 0 to 6.)

[3] The compound according to [1] or [2], wherein Ar is a condensed ring having at least one aromatic hydrocarbon ring or a group in which a plurality of aromatic rings are bonded by a single bond and at least one of the aromatic rings is an aromatic hydrocarbon ring A fluoroalkane derivative as described.

[4] The fluoroalkane derivative according to any one of [1] to [3], wherein Ar is a biphenylene group.

[5] A gelling agent comprising a fluoroalkane derivative according to any one of [1] to [4].

[6] A gel composition comprising the gelling agent according to [5] and an organic solvent.

[7] An electrode for an electrochemical device comprising the fluoroalkane derivative according to any one of [1] to [4].

[8] An electrolyte solution for a dye-sensitized solar cell comprising the fluoroalkane derivative according to any one of [1] to [4].

[9] A carbon dioxide absorbent composition comprising a fluoroalkane derivative according to any one of [1] to [4] and an ionic liquid.

According to the present invention, there is provided a novel fluoroalkane derivative capable of gelation or solidification by adding a small amount of various nonaqueous solvents, a gelling agent containing the compound, a gel composition comprising the gelling agent and a novel fluoroalkane derivative , An electrolyte solution for a dye-sensitized solar cell, and a carbon dioxide absorbent composition.

Hereinafter, a mode for carrying out the present invention (hereinafter simply referred to as " present embodiment ") will be described in detail. The fluoroalkane derivative of the present embodiment is a compound having an alkylsulfonyl group having a perfluoroalkyl group and a hydrocarbonoxy group and is represented by the above formula (1) (hereinafter referred to as "compound (1)") Is a compound in which R in the formula (1) is a group represented by the above formula (2) (hereinafter referred to as "compound (2)").

In the formula (1), Ar represents a substituted or unsubstituted divalent aromatic group having 8 to 30 nuclear atoms. The divalent aromatic group is a cyclic divalent group that exhibits so-called " aromaticity ". The divalent aromatic group may be a carbon cyclic group or a heterocyclic group. These divalent aromatic groups may be substituted by a substituent or may be unsubstituted or substituted. The substituent of the divalent aromatic group is preferably selected from the viewpoint that the introduction of the perfluoroalkyl (oligomethylene) thio group and the introduction of the hydrocarbonoxy group, which will be described later, are easily possible.

The carbon-carbon cyclic group may have 10 to 30 nucleus atoms, may be substituted by a substituent, or may be an unsubstituted unsubstituted group. Specific examples thereof include a bivalent group having a nucleus represented by a biphenylene group, a terphenylene group, a naphthylene group, an anthranylene group, a phenanthrylene group, a pyrenylene group, a chryseneylene group or a fluoranthenylene group. The carbon-carbon cyclic group may have two or more of the above-mentioned divalent groups (may be the same or different) within the range of 10 to 30 nucleus atoms.

The heterocyclic group has 8 to 30 nucleus atoms and includes, for example, a nucleus represented by a furanylene group, a thiophenylene group, a triazolene group, an oxadiazolene group, a pyridylene group and a pyrimidylene group, (Two or more of them may be the same or different) within a range of 1 to 30, inclusive.

Ar may be a group having both the carbon-cyclic group and the heterocyclic group within the range of 8 to 30 nucleus atoms.

Since Ar has a number of nuclei of 8 or more, it exhibits a high gelation ability, and the structures of R and R ¹ and the degree of freedom of carbon number selection are increased. The raw material of the compound (1) in which the number of the atoms of Ar is not more than 30 is easy to obtain and is easy to synthesize.

Among them, from the viewpoints of gelation ability and ease of synthesis, it is preferable to use, as the divalent aromatic group, a condensed ring having at least one substituted or unsubstituted aromatic hydrocarbon ring (more preferably a benzene ring) A group wherein at least one of the aromatic rings is an aromatic hydrocarbon ring (more preferably a benzene ring) is preferable. The bivalent aromatic group is more preferably a substituted or unsubstituted biphenylene group, a terphenylene group, a naphthylene group, an anthranylene group and a phenylene pyridylene group (-Ph-Py-; Ph is a benzene ring, Py is pyridine And a biphenylene group is most preferable. Examples of the substituent include an alkyl group represented by a methyl group and an ethyl group, and a halogen atom. In the present specification, the "aromatic ring" may be either a carbon ring or a heterocyclic ring.

R ¹ represents a saturated or unsaturated monovalent hydrocarbon group of 1 to 20 carbon atoms, which may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. When the hydrocarbon group is a monovalent aliphatic hydrocarbon group, it may or may not be branched. When the monovalent hydrocarbon group has an aromatic hydrocarbon group, the aromatic hydrocarbon group may or may not have a substituent. The monovalent hydrocarbon group is preferably a hydrocarbon group capable of dissolving the compound (1) in a nonaqueous solvent such as an arylalkyl group represented by benzyl group in order to dissolve the compound (1) in a nonaqueous solvent and to gel the nonaqueous solvent . If the number of carbon atoms of the monovalent hydrocarbon group is 21 or more, it becomes difficult to obtain the raw material. The monovalent hydrocarbon group represented by R &^lt; 1 > is preferably an alkyl group having 1 to 14 carbon atoms, from the viewpoints of gelation ability, ease of synthesis and handling.

R represents a saturated or unsaturated, monovalent hydrocarbon group of 2 to 22 carbon atoms having a perfluoroalkyl group, and may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. When the hydrocarbon group is a monovalent aliphatic hydrocarbon group, it may or may not be branched. When the monovalent hydrocarbon group has an aromatic hydrocarbon group, the aromatic hydrocarbon group may or may not have a substituent. The monovalent hydrocarbon group may have a perfluoroalkyl group on the main chain of the molecule, or may have a perfluoroalkyl group on the side chain. Further, the monovalent hydrocarbon group may have one perfluoroalkyl group or two or more perfluoroalkyl groups. The perfluoroalkyl group may be linear or branched. The number of carbon atoms of the perfluoroalkyl group is preferably 2 to 12, more preferably 2 to 6. Further, the perfluoroalkyl group is preferably a straight chain. The longer the perfluoroalkyl group is, the higher the gelation ability is, and the shorter the perfluoroalkyl group is, the more easily the raw material can be obtained and synthesized.

In the compound (2), Ar represents a substituted or unsubstituted bivalent aromatic group having 8 to 30 nuclear atoms. The divalent aromatic group is a cyclic divalent group that exhibits so-called " aromaticity ". The divalent aromatic group may be a carbon cyclic group or a heterocyclic group. These divalent aromatic groups may be substituted by a substituent or may be unsubstituted or substituted. The substituent of the divalent aromatic group is preferably selected from the viewpoint that the introduction of the perfluoroalkyl (oligomethylene) thio group and the introduction of the hydrocarbonoxy group, which will be described later, are easily possible.

The carbon-carbon cyclic group may have 10 to 30 nucleus atoms, may be substituted by a substituent, or may be an unsubstituted unsubstituted group. Specific examples thereof include a bivalent group having a nucleus represented by a biphenylene group, a terphenylene group, a naphthylene group, an anthranylene group, a phenanthrylene group, a pyrenylene group, a chryseneylene group or a fluoranthenylene group. The carbon-carbon cyclic group may have two or more of the above-mentioned divalent groups (may be the same or different) within the range of 10 to 30 nucleus atoms.

The heterocyclic group has 8 to 30 nucleus atoms and includes, for example, a nucleus represented by a furanylene group, a thiophenylene group, a triazolene group, an oxadiazolene group, a pyridylene group and a pyrimidylene group, And a divalent group having 2 or more (may be the same or different) within the range of 30 to 30.

Ar may be a group having both the carbon-cyclic group and the heterocyclic group within the range of 8 to 30 nucleus atoms.

Since Ar has a number of nuclear atoms of 8 or more, it exhibits a high gelation ability, and the degree of freedom of the selection width is increased with respect to the structure of R and the range of the value of m. The raw material of the compound (2) in which the number of the atoms of Ar is not more than 30 is easy to obtain and easy to synthesize.

Among them, as the bivalent aromatic group, a condensed ring having at least one substituted or unsubstituted aromatic hydrocarbon ring (more preferably a benzene ring), or a condensed ring having a plurality of aromatic rings by a single bond As the bonded group, a group in which at least one of the aromatic rings is an aromatic hydrocarbon ring (more preferably a benzene ring) is preferable. The bivalent aromatic group is more preferably a substituted or unsubstituted biphenylene group, a terphenylene group, a naphthylene group, an anthranylene group and a phenylene pyridylene group (-Ph-Py-; Ph is a benzene ring, Py is pyridine And a biphenylene group is most preferable. Examples of the substituent include an alkyl group represented by a methyl group and an ethyl group, and a halogen atom.

R ¹ represents a saturated or unsaturated monovalent hydrocarbon group of 1 to 20 carbon atoms, which may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. When the hydrocarbon group is a monovalent aliphatic hydrocarbon group, it may or may not be branched. When the monovalent hydrocarbon group has an aromatic hydrocarbon group, the aromatic hydrocarbon group may or may not have a substituent. However, the monovalent hydrocarbon group is preferably a hydrocarbon group capable of dissolving the compound (2) in a nonaqueous solvent such as an arylalkyl group represented by benzyl group in order to dissolve the compound (2) in a nonaqueous solvent and to gel the nonaqueous solvent . If the number of carbon atoms of the monovalent hydrocarbon group is 21 or more, it becomes difficult to obtain the raw material. The monovalent hydrocarbon group represented by R &^lt; 1 > is preferably an alkyl group having 1 to 14 carbon atoms, from the viewpoints of gelation ability, ease of synthesis and handling.

m represents a natural number of 2 to 16, preferably 2 to 12 natural numbers, more preferably 2 to 6 natural numbers. By adjusting the range of m to the above range, the compound (2) can attain higher gelation ability, handling property, ease of synthesis and ease of raw material availability. From the viewpoint of the gelation ability of the compound (2), p represents an integer of 0 to 6, preferably a natural number of 2 to 4.

From the viewpoints of excellent gelation ability for various nonaqueous solvents and the possibility of being stably present as a gel composition, the sum of the value of m and the number of carbon atoms in R ¹ is preferably 7 to 20, more preferably 8 to 16 , More preferably from 10 to 14, and even more preferably from 10 to 14.

The method of synthesizing the compound (1) and the compound (2) is not particularly limited, and the compound (1) and the compound (2) can be synthesized by an arbitrary method. For example, a skeleton of an aromatic group may be prepared first, followed by reaction with an alkyl chain or the like at both ends thereof. Alternatively, a chain at both ends may be prepared first, and finally, a predetermined aromatic may be synthesized.

More specifically, for example, compounds (1) and (2) can be obtained by the following synthesis method. First, a thiol compound represented by the following formula (1a) is sulfided with a compound represented by the following formula (1b) in a solvent such as dry THF in the presence of a base such as triethylamine to obtain a compound represented by the following formula ) Is obtained. In the formulas (1a), (1b) and (1c), Ar, m and p are the same as those in the formulas (1) and (2), and X ¹ represents a halogen atom .

HS-Ar-OH (1a)

C _m F _{2m +1} C _p H _2p X ¹ (1b)

C _m F _{2m +1} C _p H _2p -S-Ar-OH (1c)

Next, the compound represented by the above formula (1c) is etherified with a compound represented by the following formula (1d) in a solvent such as 3-pentanone in the presence of an alkali metal compound such as K ₂ CO ₃ , (1e). In the formulas (1d) and (1e), Ar, R ¹ , m and p are the same as those in the formulas (1) and (2), and X ² represents a halogen atom such as a bromine atom .

R ¹ X ² (1d)

C _m F _{2m +1} C _p H _2p -S-Ar-OR ¹ (1e)

Compound (1) and compound (2) are obtained by oxidizing the compound represented by the above formula (1e) with an oxidizing agent such as hydrogen peroxide in the presence of a catalyst such as acetic acid.

As such a synthesis method, for example, the synthesis method described in International Publication No. 2009/78268 can be referred to.

When Ar is a group in which a plurality of aromatic rings such as a biphenylene group, a terphenylene group, and a phenylene pyridylene group are bonded by a single bond, the compound (1) and the compound (2) can be obtained have. First, a thiol compound represented by the following formula (1f) is sulfided with a compound represented by the above formula (1b) in a solvent such as dry THF in the presence of a base such as triethylamine to obtain a compound represented by the formula ) Is obtained. Here, in formula (1f) and the formula (1g), m and p are the formula (2) that accept and, X ^3, for example a halogen atom such as a bromine atom, Ar ² has the formula (1) in the in Represents a part of the divalent aromatic hydrocarbon group constituting Ar in the aromatic hydrocarbon group.

HS-Ar ² -X ³ (1f)

C _m F _{2m +1} C _p H _2p -S-Ar ² -X ³ (1 g)

Subsequently, the compound represented by the formula (1g) is oxidized with an oxidizing agent such as hydrogen peroxide in the presence of a catalyst such as acetic acid to obtain the following compound (1h). Here, in the formula (1h), Ar ² , X ³ , m and p are the same as those in the formula (1g).

C _m F _{2m +1} C _p H _2p -SO ₂ -Ar ² -X ³ (1h)

The compound (1h) and the compound represented by the formula (1i) are reacted in a base aqueous solution such as K ₂ CO _{3 in} the presence of a palladium catalyst by Suzuki Miyaura coupling, 1) or compound (2). Here, the expression in (1i), R ¹ is as agreed in the above formula (1), Ar ³ is a portion of the divalent aromatic hydrocarbon group constituting the Ar in the formula (1), Ar ² than And Ar represents a part of Ar ² and Ar ³ bonded through a single bond.

R ¹ -O-Ar ³ -B (OH) ₂ (1i)

The compound (1) and the compound (2) of this embodiment can be used as a gelling agent for gelling a non-aqueous solvent. In particular, such compounds are advantageous in that various non-aqueous solvents can be gelled or solidified by the addition of small amounts. The gel composition of the present embodiment contains one or more compounds (1) or (2) and a non-aqueous solvent.

The nonaqueous solvent contained in the gel composition of the present embodiment is not particularly limited, but a nonaqueous solvent which is liquid at room temperature is generally used.

Examples of such nonaqueous solvents include alcohols such as methanol, ethanol, isopropanol, butanol and octanol, alcohols such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate and? -Butyrolactone,? -Valerolactone, Caprolactone, etc .; ketones such as dimethyl ketone, diethyl ketone, methyl ethyl ketone, 3-pentanone and acetone; ketones such as pentane, hexane, octane, cyclohexane, benzene, toluene, xylene, fluorobenzene and hexafluor Ethers such as diethyl ether, 1,2-dimethoxyethane, 1,4-dioxane, crown ethers, glymes, tetrahydrofuran and fluoroalkyl ethers, ethers such as N, N - amides such as dimethylacetamide, N, N-dimethylformamide, ethylenediamine and pyridine, propylene carbonate, ethylene carbonate, vinylene carbonate, fluoroethylene carbonate, diethyl carbonate , Carbonates such as methyl ethyl ketone and ethyl methyl carbonate, nitriles such as acetonitrile, propionitrile, adiponitrile and methoxy acetonitrile, lactams such as N-methylpyrrolidone (NMP) Sulfoxides such as dimethylsulfoxide, industrial oils such as silicone oil and petroleum, and edible oils.

An ionic liquid may also be used as the non-aqueous solvent. An ionic liquid is a room-temperature molten salt containing an ion combining an organic cation and an anion. The ionic liquid is characterized by flame retardancy, low explosibility, and little vapor pressure. The ionic liquid is expected to be developed for various applications because of its high conductivity of heat and ion, its ability to design physical properties by selection of ion species, and its selective and high gas absorption capacity .

Examples of the organic cations include imidazolium ions such as dialkylimidazolium cations and trialkylimidazolium cations, tetraalkylammonium ions, alkylpyridinium ions, dialkylpyrrolidinium ions, and dialkylpiperidinium ions. .

As the anion, the counter for these organic cations, for example, PF _{6 anion, PF 3 (C 2 F 5} ) 3 anion, PF ₃ (CF _{3) 3} anion, BF ₄ anion, BF ₂ (CF _{3) 2} anions, BF ₃ (CF ₃₎ anion, bis oxalate borate anion, Tf (trifluoromethane sulfonyl) anion, Nf (nona-fluoro-butane sulfonyl) anion, bis (fluoro sulfonyl) imide anion, bis (trifluoromethyl Imide anion, bis (pentafluoroethanesulfonyl) imide anion, dicyanoamine anion, halide anion, and the like can be used.

These non-aqueous solvents may be used singly or in combination of two or more.

The gel composition of the present embodiment preferably contains the compound (1) or the compound (2) in an amount of 0.05 to 10.0 mass%, more preferably 0.1 to 5.0 mass%, and more preferably 0.3 to 3.0 mass% More preferable. The compound (1) or the compound (2) tends to function more fully as the content of the compound (1) or the compound (2) due to the content of the lower limit value or more. When the content is lower than the upper limit, the economical efficiency and handling tend to be further improved. It is possible to further suppress the formation of impurities and to further prevent deterioration of the performance of the non-aqueous solvent.

The gel composition of the present embodiment preferably contains 80 to 99.95 mass% of the nonaqueous solvent, more preferably 90 to 99.9 mass%, further preferably 90 to 99.7 mass% of the nonaqueous solvent. The content of the compound (1) or the compound (2) tends to be more effectively functioned as a gelling agent when the content is above the lower limit value, have.

The gel composition of the present embodiment may contain other components in addition to the compound (1) or the compound (2) and the non-aqueous solvent to the extent that the compound (1) or the compound (2) . Examples of such components include a gelling agent, a coagulant, a thickener, a stabilizer, an antioxidant, an emulsifier, a lubricant, and a safety enhancing additive other than the compound (1) or the compound (2).

The method for preparing the gel composition of the present embodiment is not particularly limited. For example, a non-aqueous solvent, a gelling agent (that is, the compound (1) or the compound (2) It can be prepared by lowering the temperature of the mixed solution. The mixing order of the respective components is not particularly specified, but it is preferable to mix the gelling agent after preparing the solution comprising the non-aqueous solvent and the additives in advance, because the homogeneous mixture becomes easier.

The electrode of this embodiment is an electrode for an electrochemical device containing one or more compounds (1) or (2). The method of incorporating the compound (1) or the compound (2) into the electrode may be introduced at the same time when preparing the electrode active material mixture, or may be applied or coated later on the prepared electrode. The method for applying or coating the compound (1) or the compound (2) on the electrode is not particularly limited, and for example, a solution in which the compound (1) or the compound (2) is dissolved or dispersed in a solvent A slurry may be prepared and the solution or slurry may be coated or coated on the electrode by a bar coating method or may be applied or coated by a casting method. Alternatively, the solution or slurry may be applied by spraying or brushing.

By containing the compound (1) or the compound (2) in an electrode for an electrochemical device, safety, reliability and durability of the electrode and the electrochemical device equipped with the electrode are improved.

The content of the compound (1) or the compound (2) in the electrode of the present embodiment is not particularly limited as long as the function of the electrode is not impaired. The content thereof is preferably from 0.1 to 20.0 parts by mass, more preferably from 1.0 to 10.0 parts by mass, based on 100 parts by mass of the electrode active material from the viewpoints of maintaining adhesiveness and improving safety.

Examples of the electrochemical device of the present embodiment include a secondary battery and a battery represented by a lithium ion secondary battery, a capacitor and a capacitor represented by a lithium ion capacitor and an electric double layer capacitor, a fuel cell, and a power generating member typified by a fuel cell and a solar cell have. Among them, the electrode of the present embodiment is suitably used in a lithium ion secondary battery and a lithium ion capacitor. The electrochemical device of the present embodiment may have a conventionally known structure other than the electrode.

The electrolytic solution for a dye-sensitized solar cell of the present embodiment contains one or more compounds (1) or (2), and preferably also includes a non-aqueous solvent and an electrolyte. The non-aqueous solvent used in the electrolyte solution for the dye-sensitized solar cell is not particularly limited and various solvents can be used, and a solvent having a nitrile group such as acetonitrile, propionitrile, or methoxyacetonitrile is preferable, Nitrile. As the non-aqueous solvent of the electrolyte for the dye-sensitized solar cell, an ionic liquid may also be used. A variety of ionic liquids can be selected, but an ionic liquid having a cation containing an imidazolium group has attracted attention (for example, " Functional creation and application of ionic liquid " . The electrolyte is not particularly limited, and may be an electrolytic solution contained in an electrolytic solution of a conventional dye-sensitized solar cell.

The content of the compound (1) or the compound (2) in the electrolytic solution for a dye-sensitized solar cell of the present embodiment is not particularly limited as long as it does not impair the function of the dye-sensitized solar cell. The content thereof is preferably from 0.1 to 7.0% by mass, and more preferably from 0.5 to 5.0% by mass, from the viewpoint of the gelation ability and the performance as an electrolytic solution.

The carbon dioxide absorbent composition of the present embodiment is a composition comprising one or more compounds (1) or (2) and an ionic liquid. BACKGROUND OF THE INVENTION [0002] Carbon dioxide separation and recovery technology using an ionic liquid has attracted attention as an environmental technology (for example, " Separation, recovery, storage and isolation of CO ₂ " The carbon dioxide absorbent composition is capable of selectively physically absorbing CO ₂ in the vicinity of ordinary temperature and is capable of separating and recovering CO ₂ by a simple operation. A variety of ionic liquids can be used, and although not particularly limited, ions having an imidazolium moiety or an ammonium moiety as a cation are preferable. As the anion, it is preferable to contain fluorine, and more preferably bis (trifluoromethanesulfonylimide) ion. The carbon dioxide absorbing composition can be prepared by gelling an ionic liquid having a property of absorbing carbon dioxide with the gelling agent of the compound (1) or the compound (2).

The content of the compound (1) or the compound (2) in the carbon dioxide absorbing composition of the present embodiment is not particularly limited as long as it does not impair the function of the carbon dioxide absorbing material. The content thereof is preferably from 0.1 to 10.0 mass%, more preferably from 1.0 to 5.0 mass%, from the viewpoints of gelation ability, carbon dioxide absorbing ability and handling property.

The fluoroalkane derivative of the present embodiment can be gelated or solidified by adding a small amount of, for example, 10% or less to a relatively wide variety of nonaqueous solvents. In addition, the gel-like composition using the gel-like composition is difficult to transition to a sol at a relatively high temperature, and can be stably maintained for a long period of time as a gel. Further, since it does not usually have hydrogen bonding property or weakness, it ensures the function of the gelling agent even in a non-aqueous solvent and a system in which hydrogen bonds can not be stably present.

Although the embodiments for carrying out the present invention have been described above, the present invention is not limited to the above embodiment. The present invention can be modified in various ways without departing from the gist of the invention.

Example

Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples. On the other hand, the properties of the gel composition were measured and evaluated as follows.

(i) Evaluation of gelation ability

A gelling agent and a nonaqueous solvent (sometimes using an ionic liquid as a kind thereof) were mixed while heating in a vessel to form a homogeneous mixed solution, and the temperature was lowered to 25 캜 to obtain a sample solution. On the other hand, heating was carried out until the gelling agent was dissolved, and the final temperature was in the range of 70 to 100 캜. The container was allowed to stand in an environment of 25 ° C for 30 minutes, and the gelability was evaluated by confirming the fluidity at that time by vertically moving the container in a state in which the sample liquid was accommodated. And the mixture ratio of the nonaqueous solvent and the gelling agent is changed so as to obtain the lowest concentration of the gelling agent necessary to make the gel composition (the amount of the gelling agent based on the total amount of the gel composition Was determined as the gelation concentration. The lower the amount of the gelling agent, the higher the gelation ability can be said. The results are shown in Tables 1 to 3 and Table 5. On the other hand, "%" in Tables 1 to 3 and Table 5 means mass%.

(ii) Evaluation of the stability of the gel

The sample liquid containing the non-aqueous solvent (the lowest concentration of the gelling agent necessary for making the gel composition) was prepared at 25 占 폚 for 3 days, which was prepared in "(i) Evaluation of Gelation Capability" Were visually confirmed, and evaluated as follows. On the other hand, the confirmation of the fluidity was made by ascertaining the fluidity at that time by placing the container containing the sample liquid as an upside down. The results are shown in Table 4.

A: Stable as a gel even after standing.

B: After the stagnation, a small amount of non-aqueous solvent was exuded in the gel.

C: After the standing, the fluidity was re-expressed, or the gelling agent and the non-aqueous solvent were phase-separated.

(iii) Lithium Precipitation Test of Lithium Ion Secondary Battery

The lithium deposition test was conducted by fabricating a lithium ion battery which is a single-layer laminate type battery having an electrode to be described later. The battery charged to 4.2 V at a constant current of 9.0 mA was discharged to 3.0 V at 9.0 mA and charged at a constant current of 45 mA for 1.5 hours. The battery was disassembled in an atmosphere having a dew point of -60 占 폚 or less and a water concentration of 10 ppm or less. The surface of the negative electrode of the disassembled battery was observed with an optical microscope having a magnification of 2000 times, and the behavior of lithium precipitation was evaluated based on the following criteria.

A: Precipitation of lithium is not confirmed.

B: Precipitation of lithium is confirmed, but the surface of the precipitate is smooth.

C: Precipitation of lithium is confirmed, and a sharp dendrite (dendrite) is observed on the surface of the precipitate.

On the other hand, the precipitation of dendrites is a factor of the short circuit of the battery, which causes the safety of the battery to deteriorate.

(Iv) Carbon dioxide absorption capacity test

The carbon dioxide absorption capacity test was carried out at each carbon dioxide pressure by a gravimetric method using a magnet floating type balance (product name "MSB-AD", manufactured by Nippon Bells Co., Ltd.). The carbon dioxide absorbing ability was evaluated in terms of the amount of carbon dioxide absorbing capacity per unit weight converted into 25 atmospheric pressure and 1 atm.

(Examples 1 to 8 and Comparative Examples 1 to 3)

Gelation ability was evaluated by adding any one of various non-aqueous solvents shown in Tables 1 to 3 to the compounds represented by the following formulas (3) to (12). The results are shown in Tables 1 to 3.

The stability of the gel was evaluated by adding any one of various non-aqueous solvents shown in Table 4 to the compounds represented by the following formulas (4) to (12). The results are shown in Table 4.

(Examples 9 to 11)

Gelation ability was evaluated by adding any one of various ionic liquids shown in Table 5 to the compounds represented by the following formulas (3), (4) and (13) The results are shown in Table 5.

On the other hand, the compound represented by the formula (3) (referred to as the compound (3), hereinafter the same) was synthesized as follows.

First, compound (a) was obtained in accordance with the following scheme. Specifically, 15.04 g (3.17 x 10 ^-2 mol) of 2- (perfluorohexyl) ethyl iodide and 5.97 g (3.16 x 10 ^-2 mol) of p-bromothiophenol were dissolved in a 200- 4.88 g (4.82x10 ^-2 mol) of triethylamine was added to 100 mL of anhydrous tetrahydrofuran (anhydrous THF), and the mixture was refluxed in an oil bath at 84 DEG C for 20 hours. After returning it to room temperature, since the solid was confirmed in the solution, the solid was removed by suction filtration.

The filtrate was transferred to a 300 mL separatory funnel, cyclopentyl methyl ether was added, and the organic layer was washed twice with water, and an anhydrous magnesium sulfate was added to the organic layer, followed by drying. Anhydrous magnesium sulfate was removed by filtration through folding. The obtained filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanol. As a result, 12.36 g of the compound (a) was obtained (yield: 73%, melting point: 39 to 41 캜). The structure of the compound (a) was confirmed by ¹ H-NMR.

Next, compound (b) was obtained in the following scheme. Specifically, 2.75 g (2.83 × 10 ^-2 mol) of 35% hydrogen peroxide solution was added to a solution of 5.01 g (9.36 × 10 ^-3 mol) of the compound (a) in 50 mL of glacial acetic acid in a 300 mL egg plant flask, In an oil bath for 89 hours. After the temperature was returned to room temperature, 5 mL of a 20% aqueous sodium hydrogen sulfite solution was added to reduce unreacted hydrogen peroxide. At this time, a solid was already precipitated in the solution, but when 90 mL of water was added, a solid was further precipitated. After suction filtration, the solid was washed with water. As a result, 4.74 g of compound (b) was obtained (yield: 89%, melting point: 127 to 129 캜). The structure of the compound (b) was confirmed by ¹ H-NMR.

Compound (f), that is, compound (3) was obtained according to the following scheme. Specifically, 0.60 g (3.95 × 10 ^-3 mol) of 4-methoxyphenylboronic acid, 2.24 g (3.95 × 10 ^-3 mol) of compound (b) and 2 M aqueous solution of sodium carbonate 30 mL, and 40 mL of 1,4-dioxane (the amount added until the solid was dissolved) was added thereto. This palladium diacetate ^{0.13 g (5.80 × 10 -4 mol} ) to, triphenylphosphine ^{0.63 g (2.36 × 10 -3 mol} ) was added to, by the dim loss of tube attached to the flask, N ₂ atmosphere, 95 0.0 > C < / RTI > for 2.5 hours. After cooling to room temperature, 50 mL of water was added, and the mixture was stirred at room temperature for 2.5 hours. After transferring to a 300 mL separatory funnel, 80 mL of ethyl acetate as an organic solvent was added to remove the aqueous layer. The aqueous layer was extracted twice with 50 mL of ethyl acetate. These organic layers were combined, washed once with 120 mL of a saturated aqueous sodium hydrogencarbonate solution and twice with saturated brine. The organic layer was transferred to a 200 mL Erlenmeyer flask, and 0.2 g of activated carbon was added thereto, followed by stirring at room temperature for 30 minutes. Further, sodium sulfate was added, and the mixture was stirred at room temperature for 1 hour.

Celite was laid down to a depth of 1 cm in a Nutsche, and the solid was removed by suction filtration using it. The filtrate was transferred to a 200 mL eggplant flask and concentrated under reduced pressure to give a solid (c) (amount of solid (c): 2.18 g). 20 mL of petroleum ether and 30 mL of methanol were added to the solid (c), but since it was not completely dissolved, it was subjected to suction filtration to obtain a filtrate and a solid (d) (amount of solid (d): 1.24 g). The filtrate was concentrated under reduced pressure to give a solid (e) (amount of solid (e) 0.78 g). The ¹ H-NMR spectrum of the solid (d) and the solid (e) was measured. As a result, it was found that the main component of the solid (d) was the target. When the solid (d) was dissolved in chloroform, since black microcrystallization was confirmed in the solution, the solution was taken with a glass syringe and passed through a cylinder filter (pore diameter 0.45 mu m, diameter 13 mm) to remove microcrystallites. The solution passed through the filter was concentrated under reduced pressure and recrystallized with chloroform. In order to increase the yield, the filtrate after recrystallization was concentrated under reduced pressure, and recrystallization was performed twice with chloroform and ethanol. As a result of recrystallization three times in total, 0.87 g of compound (f) was obtained (yield: 37%, melting point: 187 to 189 ° C). The structure of the obtained compound (f) was confirmed by ¹ H-NMR (CDCl ₃ ) and ¹⁹ F-NMR (CDCl ₃ ). The results were as follows.

_{^{1 H-NMR (CDCl 3)}} 2.63 (2H, m), 3.36 (2H, m), 3.88 (3H, s), 7.03 (2H, d, J = 8.5Hz), 7.58 (2H, d, J = 8.5 Hz), 7.77 (2H, d, J = 8.5 Hz) 7.97 (2H, d, J =

_{^{19 F-NMR (CDCl 3)}} -126.60 (2F, m), -123.60 (2F, m), -123.34 (2F, m), -122.35 (2F, m), -114.02 (2F, m), -81.25 (3F, m) ppm

The compound represented by the formula (4) (referred to as the compound (4), hereinafter the same) was synthesized as follows. The compound (5), the compound (6), the compound (7), the compound (8) and the compound (9) were also synthesized in accordance with the synthesis method of the compound (4).

First, compound (a) was obtained in accordance with the following scheme. Specifically, 11.34 g (60 mmol) of p-bromothiophenol was added to a 200 mL eggplant flask under a nitrogen atmosphere, and 70 mL of DME was added thereto. Further, 29.86 g (63 mmol) of 2- (perfluorohexyl) ethyl iodide and 12.42 g (90 mmol) of K ₂ CO ₃ were added and the mixture was heated to 50 ° C and stirred for 3 hours. After returning it to room temperature, the solid remaining in the solution was removed by suction filtration. After the solid was removed, the filtrate was concentrated under reduced pressure. Since an oily matter having a high viscosity was obtained by concentration, it was vacuum-dried at 50 DEG C to distill off the remaining solvent and unreacted material. As a result, 32.82 g of the compound (a) was obtained. The structure of the compound (a) was confirmed by ¹ H-NMR (CDCl ₃ ).

Next, compound (b) was obtained in the following scheme. Specifically, 26 mL (300 mmol) of 35% hydrogen peroxide solution was added to a solution of 32.82 g of the compound (a) in 100 mL of glacial acetic acid in a 200 mL eggplant flask under a nitrogen atmosphere, and the mixture was stirred for 2 hours in an oil bath at 70 ° C . Water was added thereto, and the resulting white solid was filtered by suction filtration. Water was added to the solid, washed twice, and further washed with hexane one more time. Further, the compound (b) was dried at 90 캜 under reduced pressure to obtain 26.34 g (yield: 75%) of the compound (b). The structure of the compound (b) was confirmed by ¹ H-NMR (CDCl ₃ ).

Next, compound (j) was obtained in the following scheme. Specifically, 4.4 g (20 mmol) of the following compound (i) and 70 mL of 3-pentanone were introduced into a 200 mL eggplant flask under nitrogen atmosphere, stirred at room temperature, and then 4.13 g of C ₆ H ₁₃ Br (25 mmol) and K ₂ CO ₃ (4.14 g, 30 mmol) were further charged, and the mixture was refluxed in an oil bath at 120 ° C for 11 hours. After returning it to room temperature, the remaining solid was removed by suction filtration. The filtrate after the removal of the solid was concentrated under reduced pressure to obtain a dark red oil. Thus, it was vacuum dried (80 DEG C) to obtain 6.87 g of a solid compound (j) quantitatively. The structure of the compound (j) was confirmed by ¹ H-NMR (CDCl ₃ ).

Compound (k), that is, compound (4) was obtained according to the following scheme. Specifically, 2.0 g (6.58 mmol) of compound (j), 3.7 g (6.58 mmol) of compound (b), 60 mL of 1,4-dioxane and 0.295 g of palladium diacetate ), Triphenylphosphine (1.18 g, 4.5 mmol) and 2 M aqueous sodium carbonate solution (7 g of sodium carbonate dissolved in 30 mL of water). Then, a Dimros tube was attached to a branch flask, and heated to 95 캜 under a nitrogen atmosphere, and maintained for 120 minutes. Thereafter, the mixture was cooled to room temperature to confirm that it was separated into an upper layer (gel phase) and a lower layer (liquid phase). Ethanol was added to azeotropically distill water therefrom, and then the solvent was distilled off with an evaporator. After the solvent was distilled off, ethyl acetate was added to the flask, and the contents were dissolved by heating at 70 DEG C, and ethyl acetate was filtered under heating. Subsequently, the container containing the obtained filtrate was cooled to room temperature, and gelled again. Then, the resulting gel was washed three times with hexane until the supernatant liquid became transparent. The washed gel was filtered and the resulting solid was dried under reduced pressure at 70 ° C to obtain 2.38 g of a compound (k) (white solid).

The structure of the obtained compound (k), that is, the compound (4) was confirmed by ¹ H-NMR (CDCl ₃ ) and ¹⁹ F-NMR (CDCl ₃ ). The results were as follows.

_{^{1 H-NMR (CDCl 3)}} 0.92 (3H, m), 1.36 (6H, m), 1.81 (2H, m), 2.65 (2H, m), 3.35 (2H, m), 4.02 (2H, m), D, J = 8.0 Hz), 7.76 (2H, d, J = 8.0 Hz), 7.56

_{^{19 F-NMR (CDCl 3)}} -126.62 (2F, m), -123.60 (2F, m), -123.35 (2F, m), -122.36 (2F, m), -114.01 (2F, m), -81.25 (3F, m) ppm

Identified by compound 5, compound 6, compound 7, compound 8 and the compound of structure similarly to ^{(9) 1 H-NMR (} CDCl 3) and ¹⁹ F-NMR (CDCl ₃₎ . The results were as follows.

[Compound (5)]

_{^{1 H-NMR (CDCl 3)}} 0.90 (3H, m), 1.31 (10H, m), 1.83 (2H, m), 2.67 (2H, m), 3.37 (2H, m), 4.03 (2H, m), D, J = 8.0 Hz), 7.78 (2H, d, J = 8.0 Hz), 7.58

_{^{19 F-NMR (CDCl 3)}} -126.62 (2F, m), -123.60 (2F, m), -123.34 (2F, m), -122.36 (2F, m), -114.01 (2F, m), -81.25 (3F, m) ppm

[Compound (6)]

_{^{1 H-NMR (CDCl 3)}} 0.91 (3H, m), 1.42 (2H, m), 1.81 (2H, m), 2.65 (2H, m), 3.35 (2H, m), 4.03 (2H, m), D, J = 8.0 Hz), 7.97 (2H, d, J = 8.0 Hz), 7.57 (2H,

_{^{19 F-NMR (CDCl 3)}} -126.62 (2F, m), -123.60 (2F, m), -123.34 (2F, m), -122.37 (2F, m), -114.02 (2F, m), -81.25 (3F, m) ppm

[Compound (7)]

_{^{1 H-NMR (CDCl 3)}} 0.90 (3H, m), 1.82 (2H, m), 2.65 (2H, m), 3.34 (2H, m), 4.02 (2H, m), 7.00 (2H, d, J = 8.0 Hz), 7.56 (2H, d, J = 8.0 Hz), 7.76 (2H, d, J = 8.0 Hz)

_{^{19 F-NMR (CDCl 3)}} -126.62 (2F, m), -123.60 (2F, m), -123.34 (2F, m), -122.36 (2F, m), -114.02 (2F, m), -81.25 (3F, m) ppm

[Compound (8)]

_{^{1 H-NMR (CDCl 3)}} 0.92 (3H, m), 1.35 (6H, m), 1.80 (2H, m), 2.63 (2H, m), 3.35 (2H, m), 4.02 (2H, m), D, J = 8.0 Hz), 7.76 (2H, d, J = 8.0 Hz), 7.56

_{^{19 F-NMR (CDCl 3)}} -126.62 (2F, m), -124.50 (2F, m), -114.21 (2F, m), -81.45 (3F, m) ppm

[Compound (9)]

_{^{1 H-NMR (CDCl 3)}} 0.89 (3H, m), 1.35 (10H, m), 1.81 (2H, m), 2.65 (2H, m), 3.35 (2H, m), 4.01 (2H, m), D, J = 8.0 Hz), 7.76 (2H, d, J = 8.0 Hz), 7.56

_{^{19 F-NMR (CDCl 3)}} -126.50 (2F, m), -124.56 (2F, m), -124.24 (2F, m), -81.46 (3F, m) ppm

Compound (10), compound (11) and compound (12) were synthesized in accordance with the synthesis method described in International Publication No. 2009/78268. The structure of Compound (10), Compound (11) and Compound (13) was confirmed by ¹ H-NMR (CDCl ₃ ) and ¹⁹ F-NMR (CDCl ₃ ). The results were as follows.

[Compound (10)]

_{^{1 H-NMR (CDCl 3)}} 0.91 (3H, m), 1.36 (6H, m), 1.82 (2H, m), 2.57 (2H, m), 3.29 (2H, m), 4.04 (2H, m), 7.04 (2H, d, J = 8.0 Hz), 7.83 (2H, d, J = 8.0 Hz) ppm

_{^{19 F-NMR (CDCl 3)}} -126.59 (2F, m), -123.61 (2F, m), -123.32 (2F, m), -122.35 (2F, m), -114.00 (2F, m), -81.26 (3F, m) ppm

[Compound (11)]

_{^{1 H-NMR (CDCl 3)}} 0.88 (3H, m), 1.27 (14H, m), 1.81 (2H, m), 2.57 (2H, m), 3.29 (2H, m), 4.04 (2H, m), 7.03 (2H, d, J = 8.0 Hz), 7.83 (2H, d, J = 8.0 Hz) ppm

_{^{19 F-NMR (CDCl 3)}} -126.61 (2F, m), -123.63 (2F, m), -123.33 (2F, m), -122.36 (2F, m), -114.00 (2F, m), -81.24 (3F, m) ppm

[Compound (12)]

_{^{1 H-NMR (CDCl 3)}} 0.91 (3H, m), 1.35 (6H, m), 1.81 (2H, m), 2.57 (2H, m), 3.29 (2H, m), 4.04 (2H, m), 7.03 (2H, d, J = 12.0 Hz), 7.83 (2H, d, J = 8.0 Hz) ppm

_{^{19 F-NMR (CDCl 3)}} -126.49 (2F, m), -124.59 (2F, m), -114.24 (2F, m), -81.48 (3F, m) ppm

Compound (13) was synthesized according to the following scheme. More specifically, under a nitrogen atmosphere, a 100 mL eggplant-shaped flask was charged with 1-bromo-4 - [(3,3,4,4,5,5,6,6,7,7,8,8-trideca (0.0021 mol, compound (b)), 2-methoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane -2-yl) pyridine (0.5 g, 0.0021 mol), 40 mL of a 2 M aqueous sodium carbonate solution and 40 mL of 1,4-dioxane were added. Triphenylphosphine (0.34 g, 0.0013 mol) and palladium acetate (0.0754 g, 0.00034 mol) were further added thereto, followed by vigorous stirring at 95 ° C for 2.5 hours. After returning to the air atmosphere, 50 mL of water was added thereto at room temperature, and the inside was cooled by stirring for 30 minutes.

After completion of the reaction, since a solid was confirmed in the flask, ethyl acetate was added to dissolve the solid. The contents were transferred to a separatory funnel and the aqueous layer was removed. The organic layer was washed three times with 1 M hydrochloric acid, and the organic layer was washed once with water and brine, respectively. Magnesium sulfate was added to this and dried, and magnesium sulfate was removed by filtration. The filtrate was concentrated by an evaporator, purified by silica gel column chromatography, and recrystallized from ethanol to obtain 0.64 g (yield: 51%) of a solid.

The structure of the resulting compound (13) was confirmed by IR (KBr) and ¹ H-NMR (CDCl ₃ ). The results were as follows.

IR (KBr)? = 1138.0, 1151.5, 1197.8, 1209.4, 1234.4, 1294.2, 1485.2, 1606.7 cm ^-1

_{^{1 H-NMR (CDCl 3)}} 2.24 (2H, m), 3.36 (2H, m), 4.01 (3H, s), 6.88 (1H, d, J = 8.5Hz), 7.76 (2H, d, J = 8.5 (1H, d, J = 2.5 Hz), 7.83 (1H, dd, J = 8.5 Hz, 2.5 Hz), 8.00

(Example 12)

<Fabrication of positive electrode for lithium ion battery>

Lithium cobalt acid (LiCoO ₂ ) as a positive electrode active material, acetylene black as a conductive auxiliary agent, and polyvinylidene fluoride (PVdF) as a binder were mixed in a mass ratio of 89.5: 4.5: 6.0. The resulting mixture was further mixed with N-methyl-2-pyrrolidone to prepare a slurry-type solution. This slurry solution was applied to an aluminum foil having a thickness of 20 占 퐉 and a width of 200 nm and the solvent was dried and then rolled by a roll press and vacuum dried at 150 占 폚 for 10 hours to obtain a rectangular To obtain a positive electrode. On the other hand, with respect to the obtained mixture after vacuum drying, the basis weight per side was 24.8 g / cm 2 ± 3%, the thickness on one side was 82.6 μm ± 3%, the density was 3.0 g · cm 3 ± 3% The slurry-type solution was prepared while adjusting the amount of the solvent to 150 nm with respect to the width of the aluminum foil of 200 nm.

<Fabrication of negative electrode>

A graphite carbon powder (MCMB25-28, manufactured by Osaka Gas Chemical Co., Ltd.) as a negative electrode active material, acetylene black as a conductive auxiliary and polyvinylidene fluoride (PVdF) as a binder in a mass ratio of 93.0: 2.0: 5.0 Mixed. The resulting mixture was further mixed with N-methyl-2-pyrrolidone to prepare a slurry-type solution. The slurry solution was applied to an aluminum foil having a thickness of 14 占 퐉 and a width of 200 nm and the solvent was dried and then rolled by a roll press and vacuum dried at 150 占 폚 for 10 hours and punched at 52 mm x 32 mm To obtain a negative electrode. On the other hand, for the obtained electrode after vacuum drying, the basis weight per side was 11.8 g / cm 2 ± 3%, the thickness on one side was 84.6 μm ± 3%, the density was 1.4 g · cm 3 ± 3% The slurry-type solution was prepared while adjusting the amount of the solvent to 150 nm with respect to the width of the aluminum foil of 200 nm.

&Lt; Application of perfluorocarbon derivative >

Compound (4) was mixed in an amount of 5 parts by mass based on 100 parts by mass of dimethyl carbonate and dissolved at 85 占 폚 to obtain a dimethyl carbonate solution (?). The solution (?) Was applied on the anode in a heated state so that the cathode active material and the compound (4) were in a ratio of 4: 1 by mass. After the application, heating was continued from the back surface of the electrode to remove the dimethyl carbonate, thereby casting the compound (4) on the positive electrode.

Similarly, the solution (?) Was applied on the negative electrode in a heated state so that the negative electrode material and the compound (4) were 2: 1 in a mass ratio and the heating was further continued by using the solution (?) To obtain dimethyl carbonate The compound (4) was cast on a negative electrode by distillation removal.

<Battery Assembly>

Two laminate films (without drawing, thickness 120 占 퐉, 68 mm 占 48 mm) in which an aluminum layer and a resin layer were laminated were overlapped with the aluminum layer side outward and three sides were sealed to produce a laminate cell sheath. Next, a polyethylene-made microporous membrane (thickness: 20 m, 53 mm x 33 mm) was prepared as a separator, and a positive electrode and a negative electrode coated with the compound (4) as described above were alternately laminated to each other through a separator Were placed in a laminate cell enclosure. Subsequently, an electrolytic solution was injected into the shell enclosure, and the laminate was immersed in the electrolytic solution. On the other hand, the electrolytic solution was prepared by dissolving 1 M of LiPF ₆ in a mixed solution of ethylene carbonate and methyl ethyl carbonate in a volume ratio of 1: 2. The injection of the electrolyte was performed while repeating the atmospheric pressure and the reduced pressure of 100 mmHg until bubble formation was eliminated. Under a reduced pressure of 100 mmHg, the remaining one side of the laminate cell sheath was sealed to obtain a lithium ion secondary battery.

The obtained lithium ion secondary battery was subjected to &quot; (iii) Lithium Precipitation Test of Lithium Ion Secondary Battery &quot;. The results are shown in Table 6.

(Examples 12 to 14 and Comparative Example 4)

A battery was assembled in the same manner as in Example 12 except that the coating of the compound (4) was changed on each electrode, and "(iii) Lithium Precipitation Test of Lithium Ion Secondary Battery" was carried out. The evaluation results are shown in Table 6.

(Example 15)

Compound (13) was added in an amount of 5.3 parts by mass with respect to 100 parts by mass of P13 TFSI as an ionic liquid, and the mixture was heated to 80 deg. C to dissolve it, and then cooled to room temperature to prepare an evaluation sample. "(Iv) Carbon Dioxide Absorption Capacity Test" was carried out using the sample. The evaluation results are shown in Table 7.

INDUSTRIAL APPLICABILITY The fluoroalkane derivative, gelling agent and gel composition of the present invention can be used for the purpose of solidifying a liquid phase material in various industrial fields (for example, paint, cosmetics, medicine medical treatment, petroleum outflow processing, Can be used.

Claims (9)

A fluoroalkane derivative represented by the following formula (1).
R-SO ₂ -Ar-OR ¹ (1)
(Wherein Ar represents a substituted or unsubstituted divalent aromatic group having 8 to 30 nuclear atoms, R ¹ represents a saturated or unsaturated monovalent hydrocarbon group of 1 to 20 carbon atoms, and R represents a group represented by the following formula Indicates the group to be displayed.
C _m F _{2m + 1} C _p H _2p - (2)
(Wherein m represents a natural number of 2 to 16, and p represents an integer of 1 to 6) The fluoroalkane derivative according to claim 1, wherein Ar is a condensed ring having at least one aromatic hydrocarbon ring or a group in which a plurality of aromatic rings are bonded by a single bond, and at least one of the aromatic rings is an aromatic hydrocarbon ring. The fluoroalkane derivative according to claim 1, wherein Ar is a biphenylene group. 3. The fluoroalkane derivative according to claim 2, wherein Ar is a biphenylene group. A gelling agent comprising a fluoroalkane derivative according to any one of claims 1 to 4. A gel composition comprising the gelling agent according to claim 5 and an organic solvent. An electrode for an electrochemical device comprising the fluoroalkane derivative according to any one of claims 1 to 4. An electrolyte solution for a dye-sensitized solar cell comprising the fluoroalkane derivative according to any one of claims 1 to 4. A carbon dioxide absorbent composition comprising the fluoroalkane derivative according to any one of claims 1 to 4 and an ionic liquid.